臺灣博碩士論文加值系統

從台灣產番荔枝科植物刺番荔枝(Annona muricata)之種子共分離純化得到二十八個化合物，包含了：二十三個acetogenins類化合物，其中有二十個mono-THF rings acetogenins，annonacin (1)、annonacinone (2)、annomontacin (3)、cis-annomontacin (4)、xylopiacin (5)、murisolin (6)、muricatetrocin A (7) & B (8)、muricin A (9)、muricin B (10)、muricin C (11)、muricin D (12)、muricin E (13)、muricin F (14)、muricin G (15)、longifolicin (16)、corossolin (17)、corossolone (18)、muricin H (19)與muricin I (20)；一個adjacent bis-THF rings acetogenin，annocatacin B (21)；一個linear acetogenin，cohibin A (22)；一個含epoxy acetogenin，epomuricin (23)；一個amide類的化合物，N-palmitryltryptamine (24)；及四個steroids類的化合物，b-sitosterol (25)、stigmasterol (26)、b-sitosteryl-D-glucoside (27)、stigmasteryl-D-glucoside (28)。
上列二十八個化合物的結構解析經由光譜資料分析、並配合化學方法及各種衍生物的製備加以證明確定。其中，化合物4、9~15、19~22均為文獻未發表過之新化合物。化合物3、5、16與24為本植物首次分離得到，在化學成分分類學上頗具意義。
在細胞毒殺作用研究方面，所分離得到的乙醯生合成物 (acetogenins)除了化合物13、15與22之細胞毒性尚在測試中外，結果顯示除了化合物10、11與23對於人類肝癌細胞Hep G2無抑制活性外，大部份對於人類肝癌細胞Hep G2與Hep 2,2,15均有不錯的抑制活性 （IC50<4 mg/mL）。其中，化合物1、3、7~11、14與17對於人類肝癌細胞Hep 2,2,15有較佳之抑制活性，IC50值介於3.86 ´ 10-3~
5.13 ´ 10-3 mg/mL。而化合物5、12與17對於人類肝癌細胞Hep G2具非常顯著之抑制活性，IC50值分別為3.43 ´ 10-3、6.60 ´ 10-4與4.04 ´ 10-4 mg/mL。
對於本植物種子活性成分的研究中，發現許多新的acetogenins類化合物，並對其結構解析與細胞毒殺作用進行完整的探討，期望能為新藥的開發找尋新的契機。

Twenty eight compounds including twenty mono-THF ring acetogenins, annonacin (1), annonacinone (2), annomontacin (3), cis- annomontacin (4), xylopiacin (5), murisolin (6), muricatetrocin A (7) & B (8), muricin A (9), muricin B (10), muricin C (11), muricin D (12), muricin E (13)、muricin F (14), muricin G (15), longifolicin (16), corossolin (17), corossolone (18), muricin H (19) and muricin I (20), one adjacent bis-THF rings acetogenin, annocatacin B (21), one linear acetogenin, cohibin A (22), one epoxyl acetogenin, epomuricin (23), one amide, N-palmitryltryptamine (24) and four steroids, b-sitosterol (25), stigmasterol (26), b-sitosteryl-D-glucoside (27) and stigmasteryl-D-glucoside (28) have been isolated from the seeds of Formosan Annona muricata.
All isolates were characterized by spectral and chemical analysis. Among them, 4, 9-15 and 19-22 are new compounds. In addition, compounds 3, 5, 16 and 24, first isolated form the plant, are rather significant evidence in chemotaxonomy of Annonaceae.
Among these acetogenins, except compounds 13, 15 and 22, were tested for their cytotoxicity against Hep G2 and Hep 2,2,15 cell lines (human hepatoma cells). Compounds 1, 3, 7-11, 14 and 16 exhibited potent cytotoxicity against Hep 2,2,15 cell line with IC50 3.82 ´ 10-3~5.13 ´ 10-3mg/mL. In addition, compounds 5, 12 and 16 also showed significant cytotoxicity with IC50 3.43 ´ 10-3, 6.60 ´ 10-4 and 4.04 ´ 10-4 mg/mL, respectively against Hep G2 cell line.
For searching bioactive constitutents of the seeds of Annona muricata, several new acetogenins were isolated. The structural elucidation and biological activities are discussed in detail. The acetogenins could well make them become the next class of useful antitumor agents.

誌謝 I
目錄 II
圖表目錄 IV
中文摘要 1
英文摘要 3
第一章 緒論 9
第一節 前言 9
第二節 植物分佈及形態 19
第三節 研究目的 20
第二章 刺番荔枝種子成分之抽取和分離 21
第三章 化合物之結構證明 31
第一節 Annonacin (1) 之構造證明 31
第二節 Annonacinone (2) 之構造證明 36
第三節 Annomontacin (3) 之構造證明 41
第四節 cis-Annomontacin (4) 之構造證明 46
第五節 Xylopiacin (5) 之構造證明 52
第六節 Murisolin (6) 之構造證明 57
第七節 Muricatetrocin A (7) & B (8) 之構造證明 62
第八節 Muricin A (9)與B (10) 之構造證明 70
第九節Muricin C (11)、D (12) 與C (13) 之構造證明 82
第十節Muricin F (14) 之構造證明 90
第十一節Muricin G (15) 之構造證明 95
第十二節Longifolicin (16) 之構造證明 100
第十三節 Corossolin (17) 之構造證明歐……………………... 105
第十四節 Corossolone (18) 之構造證明 110
第十五節 Muricin H (19) 之構造證明 115
第十六節Muricin I (20) 之構造證明…………………………..120
第十七節 Annocatacin A (21) 之構造證明 125
第十八節 Cohibin A (22) 之構造證明 133
第十九節 Epomuricin (23) 之構造證明 138
第二十節 N-palmitryltryptamine (24) 之構造證明 143
第四章 細胞毒殺試驗 147
第五章 實驗部份 153
第一節 儀器與材料 153
第二節 植物材料與分離純化 156
第三節 衍生物之製備與研究 158
第四節 各化合物光譜數據整理 160
第六章 結論 172
參考文獻 176

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